diethyl(isopropoxy)borane | 74953-03-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: diethyl(isopropoxy)borane
• 英文别名: diethylisopropoxyborane；i-propoxydiethylborane；Borinic acid, diethyl-, 1-methylethyl ester；diethyl(propan-2-yloxy)borane
• CAS: 74953-03-0
• 化学式: C₇H₁₇BO
• 分子量: 128.022
• InChiKey: KINHWSVLCIEQTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  diethyl(isopropoxy)borane 、 异丙醇 生成 (3R,5S)-3,5-Dihydroxy-6-trityloxy-hexanoic acid allyl ester
  参考文献：
  名称：

  CHEN KAU-MING; HARDTMANN G. E.; PRASAD K.; REPIC O.; SHAPIRO M. J., TETRAHEDRON LETT., 28,(1987) N 2, 155-158

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl magnesium iodide 、 硼酸三异丙酯 以 乙醚 为溶剂， 生成 diethyl(isopropoxy)borane
  参考文献：
  名称：

  从格氏试剂和精选的三烷氧基硼烷选择性制备硼酸酯

  摘要：

  The reaction of trialkoxyboranes with ethylmagnesium bromide was investigated for the selective alkylation to the symmetrical borinic esters, R2BOR'. Triisopropoxyborane was found to react cleanly with 2 equiv of the Gringnard reagent to form diethylisopropoxyborane at -40-degrees-C. The selectivity of this reaction is largely controlled by the stability of the bromomagnesium diethyldiisopropoxyborate, MgBr[Et2B(O(i)Pr)2]. Triisopropoxyborane was found to be the most selective borane examined, yielding symmetrical borinic esters for primary and aryl derivatives with high selectivities. Secondary alkyl groups showed lower selectivities. This reaction has been developed into a general procedure for preparation of diorganyl-alkoxyboranes from readily available organomagnesium reagents, especially for those containing organic groups which are not accessible via hydroboration.

  DOI：

  10.1021/om00038a024

文献信息

• 一种合成二乙基烷氧基硼烷的工艺
  申请人：沧州普瑞东方科技有限公司

  公开号：CN106279230B

  公开（公告）日：2018-02-06

  本发明公开了一种合成二乙基烷氧基硼烷的工艺，属于硼化学合成领域。将2‑2.2当量乙基格氏试剂或乙基锂与硼化试剂反应，反应结束后淬灭，得到的中间体加入醇和脱水溶剂，精馏后得到二乙基烷氧基硼烷。该方法原料易得，操作方便，比较适合工业化放大合成。
• Organoboranes. 56. Systematic study of the reactions of 1-alkenylboronic esters with representative organolithium and Grignard reagents to provide an efficient, selective synthesis of organyl-1-alkenylborinic esters
  作者：Herbert C. Brown、Nagarajan Vasumathi、Navalkishore N. Joshi

  DOI：10.1021/om00028a021

  日期：1993.4

  A selective reaction of the ''ate'' complexes formed with 1-alkenylboronic esters and organolithium or Grignard reagents, by treatment with either Bronsted or Lewis acids at -78-degrees-C to give the corresponding organylalkenylborinic esters, is explored in this study. This systematic, detailed study reveals that the nature of the alkoxy group on boron, the nature and the amount of the alkyllithium or Grignard reagent used, the solvent, the reaction temperature, and the nature and amount of the acid used all play significant roles in influencing both the yield and the selectivity achieved for the formation of the desired organylalkenylborinates. Optimized procedures for the syntheses of representative organylalkenylborinic esters in high yield are summarized.
• PAETZOLD P.; SCHIMMEL G., Z. NATURFORSCH., 1980, B 35, NO 50, 568-577
  作者：PAETZOLD P.、 SCHIMMEL G.

  DOI：——

  日期：——